I was reading the reaction of primary nitroalkane with nitrous acid. I read this reaction enter image description here

Another mechanism which I saw:enter image description here

I am now confused whether the first mechanism occur or the second one.I tried to search it on google but didn't get anything which could clear this doubt .Please help me regarding this.This I need to know because the reaction written in my book after 2nd reaction is- enter image description here

If 1st reaction is right then what will occur after adding $\ce{NaOH}$ in the product. Also when I read Victor Mayer test the 1st reaction was written there. Due to this I am in a dilemma. Please explain.

  • 4
    $\begingroup$ It could be both. The two products can tautomerize like a ketone and an enol. $\endgroup$ Commented May 10, 2018 at 13:20
  • 7
    $\begingroup$ Yes, the two products are tautomers, so the answer is both. And that is not a "mechanism"... $\endgroup$ Commented May 10, 2018 at 14:43

1 Answer 1


As the comments say, it's both. The two products can tautomerize in the same way as a ketone and it's tautomeric enol. In fact, this is basically a keto-enol tautomerization, disguised by occurring around a nitrogen atom instead of carbon.

  • $\begingroup$ Could you please tell the mechanism of the reaction? $\endgroup$
    – Archer
    Commented Jun 21, 2018 at 6:04

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